Asymmetric synthesis of cis-2,4-disubstituted azetidin-3-ones from metal carbene chemistry

Several chiral cis-2,4-disubstituted azetidin-3-ones were prepared as single diastereoisomers from N-protected amino acids, employing a highly stereoselective copper carbenoid N–H insertion reaction of diazoketones. These azetidin-3-ones were then converted into fully substituted azetidines in a few steps in good to high yields.

Graphical abstractSeveral chiral cis-2,4-disubstituted azetidin-3-ones were prepared as single diastereoisomers from N-protected amino acids, employing a highly stereoselective copper carbenoid N–H insertion reaction of diazoketones.Figure optionsDownload full-size imageDownload as PowerPoint slide